The present invention relates to silylmethylimidazoles, and, more particularly, to silylmethylimidazoles such as (1,1'-biphenyl-4-yl)dimethyl(1H-imidazol-1-ylmethyl)silane, and to their use in controlling fungus diseases of living plants.
U.S. Pat. No. 3,692,798 discloses compounds of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 can be lower alkyl and phenyl. It is taught that the compounds are useful as antimicrobial agents. Agricultural uses are not disclosed, nor are compounds wherein R.sub.1, R.sub.2 or R.sub.3 is substituted phenyl.
European Pat. No. 29,993 discloses compounds of the formula: ##STR2## wherein R can be C.sub.1 -C.sub.4 alkyl and Y and Z can be H or SiR.sub.1 R.sub.2 R.sub.3, wherein R.sub.1, R.sub.2, and R.sub.3 can be alkyl, haloalkyl, alkenyl, alkynyl, or substituted phenyl. It is taught that the compounds are useful as agricultural fungicides.
U.S. Pat. Nos. 3,256,308 and 3,337,598 disclose compounds of the formula: ##STR3## wherein R.sub.1 can be methyl, ethyl, vinyl, or phenyl. Their use to control fungi is also taught.
Belgian Pat. No. 785,127 discloses quaternary ammonium salts such as: ##STR4## and their use as fungicides.
Research Disclosure 17,652 discloses silyl ethers of the formula: ##STR5## wherein Ar can be substituted phenyl, X can be CH or N, and R can be alkyl. It is taught that the compounds are useful as agricultural fungicides.
West German Pat. No. DE 3,000,140 discloses silyl ethers of the formula: ##STR6## wherein Ar can be substituted phenyl, X can be CH or N, and R can be phenyl or lower alkyl. It is taught that these compounds are useful as agricultural fungicides.
U.S. Pat. No. 4,248,992 discloses guanidines of the formula: ##STR7## wherein R can be H, alkyl, or alkoxy and R.sub.1 can be H or alkyl. It is taught that these compounds are useful as antifungal agents for molded plastics and rubbers.
U.S.S.R. Pat. No. 346,306 discloses silylmethylazoles of the formula: EQU (R.sub.1).sub.n (R.sub.2 O).sub.3-n SiCH.sub.2 Az
wherein R.sub.1 and R.sub.2 are alkyl groups, n is 0-3, and Az is a pyrazole, imidazole, or benzimidazole ring, optionally substituted.
U.S.S.R. Pat. No. 271,552 discloses silylethylazoles of the formula: EQU (R.sub.1).sub.n (R.sub.2 O).sub.3-n SiCH.sub.2 CH.sub.2 Az
wherein R.sub.1, R.sub.2, n, and Az are as described in the previous reference.
European Pat. No. 11,769 discloses compounds of the following formula: ##STR8## wherein R is substituted phenyl, naphthyl or tetrahydronaphthyl ring;
R.sub.1 is a substituted phenyl or cycloalkyl ring; PA1 R.sub.2 is H, or together with R.sub.1 it may form an annelated aryl or alkyl ring; PA1 R.sub.3 is halogen, alkyl, alkoxy or haloalkyl; PA1 n is 0, 1, 2 or 3; and PA1 X is CH or N, PA1 R.sub.1 is H, CN, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, optionally substituted aryl, or optionally substituted aralkyl; PA1 R.sub.2 is H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, optionally substituted aryl, or optionally substituted aralkyl; PA1 R.sub.3 and R.sub.4 are H, alkyl, alkenyl, cycloalkyl, cycloalkenyl, optionally substituted aryl, or optionally substituted aralkyl; PA1 Z is optionally substituted aryl; PA1 n is 0 or 1; and PA1 n' is 0 or 1, PA1 R.sub.1 is C.sub.6 -C.sub.18 alkyl, C.sub.3 -C.sub.6 cycloalkyl, naphthyl, or ##STR11## where R.sub.4 and R.sub.5 are independently --H, halogen, --OCH.sub.3, --OCF.sub.3, --SCH.sub.3, --SO.sub.2 CH.sub.3, --CF.sub.3, phenyl, phenyl substituted with halogen and/or C.sub.1 -C.sub.4 alkyl and/or --CF.sub.3, phenoxy, phenoxy substituted with halogen and/or C.sub.1 -C.sub.4 alkyl and/or --CF.sub.3, C.sub.1 -C.sub.4 alkyl, or cyclohexyl; PA1 with the proviso that both R.sub.4 and R.sub.5 may not simultaneously be H; and PA1 R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, OR.sub.6, or ##STR12## wherein R.sub.4 and R.sub.5 are as defined above except that R.sub.4 and R.sub.5 may simultaneously be H; and PA1 where R.sub.6 is H, C.sub.1 -C.sub.4 alkyl, or ##STR13## with the proviso that when R.sub.2 and R.sub.3 are both OR.sub.6, then R.sub.6 must be C.sub.1 -C.sub.4 alkyl; or PA1 R.sub.2 and R.sub.3 together may be a 1,2- or 1,3- or 1,4-glycol bridge or a 1,4 unsaturated glycol bridge substituted by up to four alkyl groups R.sub.7 -R.sub.10 that have a total of up to four carbon atoms ##STR14## R.sub.11 is H or C.sub.1 -C.sub.4 alkyl; and fungicidally active metal complexes or protic acid salts of said compounds. PA1 Q.sub.1 =Q.sub.2 =Q.sub.3 =H; and R.sub.11 is H or CH.sub.3. PA1 R.sub.1 is ##STR15## and R.sub.2 is C.sub.1 -C.sub.4 alkyl, phenyl, or ##STR16## and R.sub.3 is C.sub.1 -C.sub.4 alkyl or OR.sub.6, where R.sub.6 is H, C.sub.1 -C.sub.4 alkyl or ##STR17## PA1 R.sub.5 is H, F, Cl, or Br; and PA1 R.sub.2 is ##STR19## or C.sub.1 -C.sub.4 alkyl; and R.sub.3 is C.sub.1 -C.sub.4 alkyl or OR.sub.6, where R.sub.6 is H, C.sub.1 -C.sub.4 alkyl or ##STR20## PA1 R.sub.3 is OH, OR.sub.6, C.sub.1 -C.sub.4 alkyl or Cl; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl or ##STR23## R.sub.11 is H or C.sub.1 -C.sub.4 alkyl; and X is Cl, Br or I.
and their use as antimicrobials.
Belgian Pat. No. 838,298 discloses compounds of the following formula: ##STR9## where A and B are C.sub.1 -C.sub.5 divalent alkyl groups;
and their use as agricultural fungicides.